


Whipping Boy

by sydwtr



Category: Critical Role (Web Series)
Genre: Aftercare, BDSM, BDSM as coping, Caning, F/M, Flogging, Safe Sane and Consensual, Spanking, handjob
Language: English
Status: Completed
Published: 2018-12-14
Updated: 2018-12-14
Packaged: 2019-09-14 08:11:09
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 2,208
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/16909326
Author URL: https://archiveofourown.org/users/sydwtr/pseuds/sydwtr
Summary: For the first time in a long time, Caleb asks for help.





	Whipping Boy

His back is a nightmare of old scars and Jester chews her lip, her hand trembling as she reaches out to touch him. “We don’t have to do this, Caleb.”

Under her touch, his breath hitches, his hands clenching into fists at his sides. He asked for this. He asked for something to… to… he’s not even sure, anymore, what this is supposed to do. Make the nightmares stop? Make the bone-deep ache he feels when he wakes in the morning go away? This won’t do any of that… But he needs it. He needs to be punished for what he’s done, for what he’s failed to do.

That’s too hard to articulate.

“ _Ja_ , I know, but it will be fun.”

Her hand trails over his skin, down to the curve of his hip and around him, back up his torso. Blue fingers trail into the thick dark hair on his chest, settle over his pounding heart. He feels warmth and fuzziness in his head for half a second before clarity returns.

“Why do you want me to do this to you?”

“I…” The lie falters and he shoots a glance over his shoulder with a frown, turns back from her gaze quickly. Magic, of course. “I don’t want to tell you the whole story.”

“Do you think it will help you?”

“I do.”

Jester hums, leans in and kisses his shoulder. “Okay, then. Tell me the things you want me to do to you.”

He outlines the basics, chooses his words carefully. It’s not explicitly sexual… but there’s a stirring thrill as he details the punishment he must endure to her. Something that claws up from inside him and tries to pry itself out of his loosened vocal cords. Memories he’s buried deep, not of the act but of the afterwards, of the… the…

“...and taking care, afterwards,” he finishes, looking down, hoping he won’t have to explain further. Not sure he’s able to, even with magic drawing truths from him.

He can feel her smile against his skin, her mouth trailing from his shoulder to his neck, gentle kisses that leave him shivering. “Taking care, of course.” The headiness returns for a moment before fading again to clarity as the spell is dispelled. Jester lingers on him in gentle movements, her hands positioning him as she wants him. No restraints needed, he’ll behave and take his punishment, so she braces his hands on the wall and bends him forward slightly. Her touch lingers on the waistband of his trousers, fingers dipping in gently before she steps away.

There’s the lightest sound of his breathing under her footsteps, rapid and shallow in anticipation. Whatever sort of scene she wants to set up, whatever reason she wants to give for why this is happening to him, he’s left in her hands. If she even wants to set a scene, rather than just delivering the pain he deserves to him without reason. He has a long enough list of transgressions that he can come up with a reason.

The cane taps lightly on the floor as she comes back and he flinches involuntarily. His fingers curl against the wall, his muscles tensing as he prepares for the blow that’s to come. He’ll be sobbing apologies in minutes, begging forgiveness and promising to never do it again, reduced from a bright scholar to a sniveling child--

“Give me a color before we start, Caleb.” Her tone is still soft, but there’s an underthread of _command_ to it, a different kind of magic.

He swallows, his muscles stiffening for a moment, before relaxing. “ _Grün_.” It’s easier in Zemnian, a seeping of reality. He wasn’t allowed to speak the language of his parents in… before.

One last light kiss to the bare skin high on his back, before Jester’s open palm strikes him through his trousers. Caleb hisses in a sharp breath, the pain nothing compared to the emotional impact, the dredging up of old humiliations and fears and it all fades away as she strikes him again.

“Do you know…” Jester’s fingers trail rapidly up his back and down again, her open palm hitting him once more, “that you deserve this?”

“I… I do--mmph.” Answering is difficult, the noises that want to escape him when her hand delivers another blow trying to take over his composed words.

Five and she lets him rest, reaches up and brushes his hair lightly off his forehead. “Why do you deserve it?”

It’s easier to admit, now that it’s happening. Truths spill from Caleb’s lips between hits, things he’s done wrong. Wrong by her, wrong by the group, wrong by himself, wrong by the world. Things he’d never admit in any other setting. By the time she lets him rest again, he’s nearly sobbing. _And it’s only just beginning_ , a part of his mind whispers.

Jester wraps her arms around him from behind, holds him close to herself and presses her chest to his back. “I forgive you, you know. But you don’t forgive yourself, do you?”

“ _Nein_ …”

“Then we’ll work on that. Give me a color.”

The rest periods make it easier, the moments between when she holds him, talks to him in soft words and touches him with gentle hands. Caleb exhales slowly, feels the world resettle around him. “ _Grün_.”

“Are you okay with me using the cane?”

“ _Ja_ , that… that’s fine.” The cane is a relic from _before_ , the usual implement of punishment. Rapped across his knuckles for minor misbehaviors, poked into the middle of his back for poor posture, swatted against the backs of his legs for failure to comply. He knows how it will feel against him, the sharp stinging line of impact that tells him he’s done wrong. He needs the bruises that linger for days and tell him in no uncertain terms that he’s a failure.

Jester barely taps him with it on the first, lets him brace for the incoming impact. Even through his trousers it smarts as it cracks across his ass, the familiar line of stinging pain followed by low heat. His breath catches in his throat, his eyes welling with unexpected tears.

“Please, _bitte_ , I’m so--” Another impact, over the same spot, followed by the clap of her hand against it. Caleb chokes on a sob, his short nails scrambling against the wall.

“ _Grün_?” Jester asks against his ear, her hand rubbing down his spine slowly.

“ _Grün_ ,” he agrees, gasping in a breath and letting it out slowly. “ _Grün_ … Continue?”

He can’t stop how strong his reactions are to the impacts, he can’t stop the tears that track down his face, nor the pleas that fall from his lips. First apologies, then choked begging for forgiveness, then finally, as Jester swings the cane against the backs of his thighs with too little force to hurt but too much consistency to be ignored, he starts listing off his wrongdoings.

She sets the cane against the wall as he runs out of wrongs, as he leans into the wall gasping for breath, and gently tracks her hands down his back, across the backs of his thighs. A low level healing spell, just enough to take the sting out, pools warmth over his skin and Caleb leans into her, slowly brings his emotions back under control.

“I’m not done yet,” he whispers, his head falling low between his shoulders, the tension starting to climb into his back again. “I haven’t repented yet…”

“Caleb…” She wraps her arms around him, presses herself tight against his back and holds him close. “Wasn’t that punishment enough?”

“No, not yet.” His ribs expand with a rough inhale under her hands, his body shaking as he exhales. “Please…”

“Give me a color first.”

“ _Grün_. Everything is okay. I am… mmph…” Some of the tension bleeds away as she trails light kisses over his shoulder, presses her forehead to his bared skin and holds him for another minute. “This next part is… different from before.”

Jester nods against him, stepping back slowly, taking the cane with her and going to get her last implement. The gentle _whish_ of it singing through the air before it thuds against her palm makes him shiver with anticipation, arousal once more stirring in his pants. Punishment.

The ends of the falls trail up his back, starting low and climbing, making him squirm with sensation. Jester pulls it back, delivers light blows like wings against his shoulder blades before hitting firmer directly between them.

He falls into the rhythm of it easily, the not-quite-pain of the hits across his back. Her focus is higher than the open-palm spankings or the blows of the cane, across his shoulder blades, occasionally letting the falls lick around his torso to the front. Caleb hisses in a breath as Jester fans out the hits, spinning the flogger and letting just the tips of the falls kiss against his skin, like scratches from fingernails.

She stops when his skin is red and sensitive, leans into him with more gentle kisses, more soft words. Her hands trail up his arms and guide them down, hold his wrists as she wraps him into a hug against herself.

“Does it feel better, Caleb?”

“ _Ja_ , yes, it…” It’s quiet in his mind, not screaming with guilt he can’t ever be free of. The unrestful spirits of his crimes have at least been pushed back for a time. “Thank you, Jester.”

“Any time.” Her hands slide down his sides, brush over the front of his pants gently, cup the erection straining there that he’s barely noticed. “Do you want me to…?”

“Mmph…” His hips rock into her hand, his eyes closing. Caleb nods slowly, whines in the back of his throat when her hand doesn’t move. “I want you to, yes, please.”

“Good boy.” He’s not sure if it’s the words that send a shock through him, or the sensation of her hand squeezing him through his pants. Jester works the buttons open quickly, delves her hand inside and wraps her fingers carefully around him. “Such a good, good boy,” she whispers, stroking him slowly, letting him rock his hips into her touch. The praises raise a flush on his chest, his head tipping down with embarrassment. “You took your punishment so well, you deserve a reward. You deserve something nice, Caleb. Let yourself feel good, now.” Her hand moves faster with the words, thumb rubbing over the leaking head of his cock, her mouth so close and warm next to his ear. “You can cum when I tell you to, right?”

“Y-yes, ma’am…” He stutters on the words, sucks in a breath and lets it out in an unexpected, unashamed moan as Jester squeezes his cock again.

“Of course you can, my good, good boy. Ready now?” He whines against his clenched teeth, nods quickly. “Three… two… one… cum for me, Caleb. Let it feel good.”

It’s so much better than the orgasms he’s had before, with his right hand wrapped around himself and his teeth sinking into the knuckles on his left hand. Caleb doesn’t try to hide his moans, doesn’t feel the burn of shame that he has to do this, doesn’t worry about the mess he may or may not make. He cums, rocks his hips into Jester’s hand as she strokes him through it, and finds himself still seeking the pleasure when he’s empty and oversensitive, still jerking into her still hand when all it does it make him ache.

She pulls back slowly, eases him across the room to the bed and helps shed his trousers the rest of the way. Jester disappears for a moment and Caleb squints, looks around to find her before she’s back by his side, slowly cleaning up the sweat and cum on him with a warm, damp cloth. She lies in bed next to him, propped up on one arm, gently stroking his hair with her free hand. “Was that good? Was it what you needed?”

“It was… good. It helped… It…” He leans into her touch, his eyes closing. “The things I said--”

“I won’t hold what you say in the moment against you. But if you want to talk about them some other time, we can.” Jester leans in, kissing his forehead gently. “I’m glad you asked me for this.”

“You seemed the most… experienced in this field.”

“I mean, probably. I’m, like, the best at sex in our group.” Her grin draws his own mouth into a twitch of a smile, her lips pressing to his briefly in reward. “Rest up, now, Caleb. I’ll stay here.” She giggles, her eyes lighting up with girlish glee. “But gosh, won’t everyone know that we _slept together_ if you stay the whole night here? That could be a scandal.”

“I have seen Fjord leave your room in the early hours of the morning more times than I care to count, Jester.” Caleb huffs, pulling her down to lie next to him. “If it is you and me one night, no one will bat an eye.”

The stillness and silence of sleep holds them for so long, Caleb’s sure she’s actually asleep when he opens his eyes again. He leans in, kissing her forehead gently. “ _Danke_ …”


End file.
